"Turpentine Finance" with Sasha Orloff | Startup Finance, Leadership, CFO Strategy

In this conversation, Steve Love, a seasoned CFO with over $1 billion raised from VCs and $2 billion in M&A transaction experience, pulls back the curtain on high-stakes M&A. Love shares his insights from overseeing complex acquisitions like Heap's purchase of a complementary "session replay" company and Heap's eventual sale to ContentSquare. He candidly discusses navigating challenges, aligning stakeholders, prepping for diligence, and making strategic M&A decisions as a CFO. Whether you're a CFO, finance professional or simply M&A-curious, Love's tactics for evaluating targets, modeling forecasts, negotiating terms, and executing integrations provide a rare behind-the-scenes look at what it really takes to architect successful transactions. SPONSORS: 📊 Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. BEEHIIV 🐝 Power your newsletter with Beehiiv, the newsletter platform built for growth. Connect with premium brands, scale your audience, and deliver a beautiful UX that stands out in an inbox. Head to https://Beehiiv.com and use code "MOZ" for 20% off your first three months --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. Profiled this season: Databricks, Reddit, Twilio, Copart + more. Spotify: https://open.spotify.com/show/0epyYBAxLeF0PsNagdDJAJ Apple: https://podcasts.apple.com/us/podcast/company-breakdowns/id1743119197 --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://sift.com/ X/SOCIAL: @sashaorloff (Sasha) @SteveLoveCFO (Steve) TIMESTAMPS: (00:00:00) Intro and preview (00:01:24) Steve Love's impressive background (00:02:39) Diving into M&A: When and why to acquire (00:03:34) Case study: Heap's product acquisition (00:05:17) Evaluating market players and integration challenges (00:08:20) Operational considerations post-acquisition (00:10:22) The role of the CFO in M&A (00:13:29) Integration and transition best practices (00:17:43) Sponsor: NetSuite | Attio (00:20:21) The biggest surprise after acquisition (00:22:33) The first thing CFOs do after signing (00:24:34) Acquihire vs. product acquisition (00:32:29) Sponsor: Beehiiv | Brave (00:33:02) Negotiating severance packages (00:35:02) Pre-negotiating terms at hiring (00:37:34) Executing a sell-side transaction (00:37:55) Handling market checks and bankers (00:39:26) Preparing for M&A discussions (00:43:10) Navigating first meetings with acquiring CFOs (00:45:01) Challenges in cross-border acquisitions (00:49:52) Differences between private and public company sales (00:53:08) Maximizing buyer interest and value (00:55:23) Lessons from previous M&A experiences (00:58:36) Career reflections and advice for aspiring CFOs (01:02:13) Biggest misconceptions about a CFO's role (01:03:03) Wrap

How do you navigate the tide turn when your competitor collapses during one of the biggest banking crises in recent history? In this conversation, Sasha Orloff sits down with Immad Akhund, founder and CEO of Mercury*. Immad pulls back the curtain on the chaos and critical decisions made when Silicon Valley Bank fell. From mobilizing an all-hands effort to rapidly onboard new customers to developing new product features virtually overnight to instill confidence, Immad provides an unvarnished look at crisis management and steadfast leadership during turbulent times. He also shares insights on Mercury's customer-first approach to building, how rising interest rates transformed their business model, and how he thinks about investing in new product initiatives by allocating internal resources like venture investments. *Mercury is a financial technology company, not a bank. Banking services provided by Choice Financial Group and Evolve Bank & Trust, Members FDIC. --- SPONSOR: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. Profiled this season: Databricks, Reddit, Twilio, Copart + more. Spotify: https://open.spotify.com/show/0epyYBAxLeF0PsNagdDJAJ Apple: https://podcasts.apple.com/us/podcast/company-breakdowns/id1743119197 --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://mercury.com/ --- X/SOCIAL: @sashaorloff (Sasha) @Immad (Immad) --- TIMESTAMPS:

In this conversation, Sasha Orloff sits down with Steve McLaughlin, CEO and Managing Partner of FT Partners. Steve provides an insider’s look into the high-stakes world of capital raising and dealmaking for high-growth private companies. From being Goldman Sachs’ Former Head of Fintech to founding FT Partners, a global fintech investment firm, McLaughlin shares his strategies for crafting compelling narratives that unlock massive fundraising rounds - like the $33 billion valuation for Revolut and a $100 million plus raise for Sam Altman’s Worldcoin. They dive deep into storytelling, the importance of product over marketing spend, founder red flags, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://ftpartners.com/ X/SOCIAL: @sashaorloff (Sasha) @FTPartners (Steve) TIMESTAMPS: (00:00:00) The art of storytelling in high-growth company valuations (00:01:31) A capital whisperer's journey (00:02:26) Inside FTPartners: Shaping the fintech universe (00:04:33) The intricacies of capital raising and M&A (00:07:39) Crafting the perfect capital raise story (00:14:13) The complex world of investor networks (00:16:41) Maximizing value beyond valuation (00:19:05) A deep dive into successful storytelling and strategic selling (00:22:57) The philosophy of business growth and valuation (00:23:33) Understanding the founder's journey and ambitions (00:24:32) The role of investment bankers in raising capital (00:25:46) The importance of choosing the right banker (00:28:17) Revolut's success story: A case study (00:36:07) Strategic advice on growth vs. profitability (00:39:01) Reflecting on capital raising experiences and red flags (00:41:06) The evolution of FT Partners (00:46:12) Closing thoughts and acknowledgements

Ever wondered what the financial operations look like when you have billions in AUM at a top-tier VC firm? In this episode, Sasha sits down with Mark Allen, CFO at General Catalyst. Mark discusses the non-obvious complexities of managing billions in assets across hundreds of portfolio companies, from capital reserve strategies, geographical breakdowns, to reporting requirements. He shares candid insights on navigating intense moments like the Silicon Valley Bank collapse, tech innovations being adopted by VC firms, how being a fund’s CFO comprises two roles of being CFO of a fund and a firm, advice for CFOs coming to pitch at General Catalyst, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://www.generalcatalyst.com/team/mark-allen X/SOCIAL: @sashaorloff (Sasha) @generalcatalyst TIMESTAMPS: (00:00) Preview + Intro (02:37) Mark Allen’s Journey to Being CFO of General Catalyst (GC) (06:23) How the VC business model works (08:44) Power law and reserves (08:44) FP&A at a fund and capital reserve strategies (11:20) Investment mix / geographical jurisdictions (14:05) How GC maintains line of sight into their portfolio companies (14:51) Sponsor: Attio (17:04) Tools that Mark uses and revolutions in tools for CFOs (19:12) Using AI for DDQs (21:23) Inflection points in GC’s history (24:19) Transition from hundreds of millions to billions of dollars in AUM (26:01) Critical decision points for GC and Mark (30:14) Sponsor: Turpentine (30:58) Advice for CFOs on building trust with their leadership (33:03) The importance of relationships as a CFO (36:20) How General Catalyst’s work culture has changed after the pandemic (39:18) Biggest misconceptions about being CFO at VC fund (41:26) Advice for CFOs pitching to VCs (42:26) Wrap

Get an inside look at Runway - the visually stunning finance platform that's breaking conventions and captivating users with its approach to making finance fun again. In this interview, founder and CEO Siqi Chen shares the arduous 3-year journey of iterating on the product from its inception during a meeting with the a16z team, working alongside early design partners, and the key inflection points that transformed Runway into what it is today. He emphasizes the importance of storytelling, having the data from different company functions centralized and in communication with each other, and fostering a culture where work, and finance in particular, is genuinely fun. Whether you're in finance or appreciate great product design, this is a must-watch episode. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS MENTIONED: Runway Financial: https://runway.com/ Sandbox VR: https://sandboxvr.com/ X/SOCIAL: @sashaorloff (Sasha) @blader (Siqi) @runwayco (Runway) TIMESTAMPS: (00:00) Introduction to Runway and Siqi Chen (01:30) Background and Inspiration for Runway (08:25) Challenges and Pivot during COVID-19 (12:29) Raising Capital and Product Iteration (14:57) Sponsor: Attio (16:25) Balancing Feature Parity and Novelty (17:30) arly Design Partners and Customers (19:36) Building an Audience and Storytelling (23:01) Mission and Vision of Runway (26:13) Convincing Users to Leave Excel (38:05) Demo of Runway (41:45) Development and Design Process (42:49) Product Features and Future Plans (44:43) Company Culture and Team (46:45) Future of Runway

In this episode, Sasha sits down with Razzak Jallow, CFO at FloQast, to discuss the evolving role of the modern CFO as a strategic partner across the organization. They dive into how he builds trust with the CEO, his approach to fostering product innovation responsibly, and why he turned down a financing round that would have doubled FloQast's valuation. Razzak also offers advice for aspiring CFOs on evaluating their first CFO role, skills like "precision Q&A", and hiring great talent This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- X/Twitter: @sashaorloff (Sasha) @floqast (Floqast) @turpentinemedia TIMESTAMPS: TIMESTAMPS: (00:00) Preview (02:22) How Razzak would describe the role of CFO (02:55) Razzak’s superpowers: hiring and working with different people (04:28) Building trust with different colleagues across different functions and cultures (06:31) How to be the office of “how to” rather than “no” (08:47) Having an effective discussion when there isn’t a right answer (11:47) Changing the culture from being a no shop to a let’s be a partner shop (14:26) Precision Q&A (15:24) Sponsor: Attio (17:22) What is FloQast (19:34) Taking on the first CFO role and evaluating fit (21:45) Deciding not to raise at a higher valuation and why (25:20) Having a cash war chest (27:02) Balancing product innovation and financial discipline as CFO (30:00) The early milestones in a new product that unlock more capital (31:32) Getting alignment on what payback on a new product should be (38:16) Advice to future CFOs and an underrated skill people should work on more (41:39) Building trust with your CEO (45:27) Wrap

Ever wonder what it's like to get a call from Elon Musk, wanting to buy your company? In this episode, Sasha sits down with serial entrepreneur Chris Bakke to find out. Chris is the co-founder behind several successful startups, including Laskie, which was acquired by Elon Musk's X, and Interviewed, acquired by Indeed. Chris shares insights on: building a content-driven growth strategy as a founder that's led to his 200k+ follower base, navigating the M&A process and negotiating a deal directly with Musk, transitioning from founder to his current role in building X's job search platform, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- X/Twitter: @sashaorloff (Sasha) @chrisjbakke (Chris) @turpentinemedia TIMESTAMPS: (00:00) Chris Bakke Intro (02:49) Laskie and what got Chris excited about it (04:03) Content as a growth strategy (07:29) How Chris found his content voice (12:50) What’s the next thing in content (19:32) Best practices as a founder to set up M&A as a future path (24:36) Getting Indeed as a partner, investor, and acquirer of Interviewed (26:51) Laskie’s M&A Story (29:13) How Chris ended up talking to Elon about Laskie and Twitter recruiting (35:11) What Chris would’ve done differently at Indeed (37:12) Common mistakes and misconceptions during the M&A process (45:00) Chris’ most memorable X post, not of his own (46:22) Wrap

In this episode, Sasha sits down with Sagar Sanghvi, Current Partner at Accel and former CFO at Instacart. They discuss how Sagar drove the change in financial culture at Instacart and adapted rapidly to Whole Food’s acquisition by Amazon, scaling Instacart during the COVID pandemic, the balance between growth at all costs and unit economics, Sagar’s transition from CFO at Instacart to being Partner at the venture firm Accel, and much more. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: https://www.accel.com/people/sagar-sanghvi X/SOCIAL: @sashaorloff (Sasha) @spsanghvi4 (Sagar) @turpentinemedia CONTACT: sps@accel.com TIMESTAMPS: (00:00) Preview and Intro (02:30) Sagar's time at Instacart (04:29) Training from Goldman and KKR (06:58) When to transition to unit economic focus instead of growth at all costs (08:31) The process of changing a financial culture at a company (10:57) Advice for CFOs in driving culture with a founder where financial discipline is not present yet (13:39) Sponsor: Attio (14:55) How do you bring colleagues from other functions into alignment (17:22) Amazon's acquisition of Whole Foods and Instacart's internal dynamics (20:17) Signs that Amazon's acquisition of Whole Foods was a positive infection for Instacart (21:43) Instacart's wartime and tactical parts of Sagar's job during wartimes (24:04) Size of Instacart's finance team (25:10) What Sagar would have done differently in response to the acquisition (27:54) Sagar's VP of Strategy transition to CFO at Instacart (30:13) Balancing growth versus profitability (36:27) Instacart during COVID and lockdown (40:41) Sagar's transition to Accel and VC (44:59) Advice for CFOs positioning themselves to VC (47:34) What gets Sagar excited about a deal? (49:58) Wrap

In the debut episode of Turpentine Finance, host Sasha Orloff sits down with Casey Woo, Founder of Operator's Guild, GP at Fog Ventures, and WeWork's former Global Head of Strategic Finance. They unpack the value of being a business-first CFO, the lessons learned from working in pressure-cooker settings like WeWork, how CEOs can evaluate CFOs (and vice versa), and frameworks for being a career 'specialist generalist'. This show is a part of the Turpentine podcast network. Learn more: www.turpentine.co --- SPONSORS: Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine --- Recommended Podcast: Company Breakdowns Each episode of Company Breakdowns dives into S-1s and series B-and-beyond companies, interviewing founders and investors to break down the companies. First episode is on Rubrik - which just IPO'd. Coming up this season: Databricks, Reddit + more, Spotify Apple --- This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co. --- LINKS: Operator's Guild: https://operators-guild.com/ Fog Ventures: https://www.fog.ventures/ Casey's Linkedin: https://www.linkedin.com/in/caseywoo Casey's contact: hello@operators-guild.com --- X/Twitter @sashaorloff (Sasha) @caseyswoo (Casey) @FogVentures (Fog) @turpentinemedia --- TIMESTAMPS: (00:00) Preview (02:00) Life as a banker (04:06) Story following numbers or numbers following story (04:39)How banking prepared Casey for working in a startup's finance team (07:00) Deciding that working in a startup is a right fit (09:10)Hiring a CFO (11:20) Advice for bankers transitioning to operating roles (12:41) First things to accomplish when stepping into a role (14:05) Sponsor: Attio (14:52) Interview question to see if a founder takes finance seriously (16:16) Advice for CFOs to change the dynamic that finance has in the company (18:08)Casey's time at WeWork as CFO for Western US and Canada (22:00) Casey's experience being Global Head of Strategic Finance at WeWork (29:40 Advice for founders in dealing with different growth or recessive cycles (32:57) Probabilities (34:00) Time spent on fundraising vs supporting the founder as a CFO (35:26) Operator's Guild and Generalists (42:00) How can operators thrive in a transition role (47:28) The number one piece of advice Casey would give to CFOs (49:38) Wrap